Palladium-Catalyzed Carbonylative α-Arylation of tert-Butyl Cyanoacetate with (Hetero)aryl Bromides
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- 作者：Mikkel T. Jensen ; Martin Juhl ; Dennis U. Nielsen ; Mikkel F. Jacobsen ; Anders T. Lindhardt ; Troels Skrydstrup
- 刊名：Journal of Organic Chemistry
- 出版年：2016
- 出版时间：February 19, 2016
- 年：2016
- 卷：81
- 期：4
- 页码：1358-1366
- 全文大小：497K
- ISSN：1520-6904
文摘
A three-component coupling protocol has been developed for the generation of 3-oxo-3-(hetero)arylpropanenitriles via a carbonylative palladium-catalyzed α-arylation of tert-butyl 2-cyanoacetates with (hetero)aryl bromides followed by an acid-mediated decarboxylation step. Through the combination of only a stoichiometric loading of carbon monoxide and mild basic reaction conditions such as MgCl2 and dicyclohexylmethylamine for the deprotonation step, an excellent functional group tolerance was ensured for the methodology. Through the use of 13C-labeled carbon monoxide generated from 13COgen, the corresponding 13C-isotopically labeled β-ketonitriles were obtained, and these products could subsequently be converted into cyanoalkynes and 3-cyanobenzofurans with site specific 13C-isotope labeling.